Potassium Carbonate → HCID 58026149, compound

HRID 2387308Notes

Reaction equation

HRID 2387308 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:32])([CH3:31])[CH2:21][C@:22]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH2:23][CH:24]=O)=[C:16]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:32])([CH3:31])[CH2:21][C@@:22]([C:26]([F:29])([F:28])[F:27])([OH:30])[CH2:23][C:24]#[CH:1])=[C:16]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58026147HCID 58026147, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 58026149HCID 58026149, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of (1-diazo-2-oxopropyl)phosphonic acid dimethyl ester (12.5 g, 0.065 mol) and (R)-5-(4-chloro-2-methanesulfonylphenyl)-3-hydroxy-5-methyl-3-trifluoromethylhexanal (20.5 g, 0.054 mol) in 150 mL of dry MeOH was added potassium carbonate (13.8 g, 0.100 mol) at room temperature. The reaction was stirred overnight. The reaction was diluted with 200 mL of water and extracted with diethyl ether. The organic layers was washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated in vacuo. The crude material was eluted through a plug of silica using 20-25% diethyl ether/hexanes to provide (S)-6-(4-chloro-2-methanesulfonylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (18.5 g, 89%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layers was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. washThe crude material was eluted through a plug of silica using 20-25% diethyl ether/hexanes

Sources & evidence

ORD record
ord-1c1a6cfcaebf4e02b9b56625448f4e01
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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